m-Chloroperbenzoic acid → 3-(tert-butyl-5-fluoro-6-(methylsulfinyl)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

HRID 74959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74959
[C:1]([C:5]1[C:10]([F:11])=[C:9]([S:12][CH3:13])[N:8]=[C:7]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[C:10]([F:11])=[C:9]([S:12]([CH3:13])=[O:32])[N:8]=[C:7]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([Cl:23])[CH:21]=3)[NH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 672859433-(tert-butyl-5-fluoro-6-(methylthio)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine2×

Produkt 1

HCID 672858693-(tert-butyl-5-fluoro-6-(methylsulfinyl)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To the solution of 3-(tert-butyl-5-fluoro-6-(methylthio)pyrimidin-2-yl)-5-chloro-1H-pyrrolo[2,3-b]pyridine, 40b, (0.05 g, 0.11 mmol) in CH2Cl2 (3.4 mL) was added mCPBA (0.02 g, 0.11 mmol). The reaction mixture was stirred for 1 h. The reaction mixture was diluted with CH2Cl2 (10 mL) and saturated NaHCO3 solution (5 mL). The aqueous layer was extracted with CH2Cl2 (10 mL). The combined organic phases were washed again with aqueous saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo to afford the desired product that was used without further purification.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with CH2Cl2 (10 mL)
  2. washThe combined organic phases were washed again with aqueous saturated NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-346d0fdb29a7443a9b5e2d8cee39ac3f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829007B2

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